


You're Late

by quantumoddity



Series: Widomauk Courtesan AU [2]
Category: Critical Role (Web Series)
Genre: Courtesan AU, First Meetings, First Time, M/M, Sex Work, Trans Mollymauk Tealeaf, Vaginal Fingering
Language: English
Status: Completed
Published: 2019-08-10
Updated: 2019-08-10
Packaged: 2020-08-14 15:41:34
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,737
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20194672
Author URL: https://archiveofourown.org/users/quantumoddity/pseuds/quantumoddity
Summary: Mollymauk Tealeaf has a new client





	You're Late

“You’re late.”

Molly paused at the foot of the winding staircase and flashed Yasha a grin, a smooth, affable grin meant to distract from the fact that yeah, he was abominably late for work. 

“I’m not late unless someone catches me and proves I wasn’t down here fifteen minutes ago.” 

Yasha gave a derisive snort. She’d seen that grin far too many times, it had long ago lost it’s effect. “You were meant to be here half an hour ago.”

She leaned back into the shadows at the juncture of the walls, where she spent her nights on duty. Her quiet, looming presence was more than enough, most of the time, to discourage any patrons from making trouble, from treating the workers with anything less than perfect politeness. And for the rare occasions it wasn’t enough, that was what the sword slung across her back was for, glinting menacingly over the rise of her shoulder. 

“Well…if anyone asks I was here talking to you, right?” he grinned hopefully at his friend. 

“Not a chance, friend,” Yasha closed her eyes. To someone who didn’t know her, apparently sleeping on the job. But Molly knew it was so she could better hear the conversations drifting in from the bar, buoyed rather than muffled by the tasteful music, listening for any turning south. Most times she would appear, silent and foreboding, seconds after a patron had said something unkind or made a threat but before they’d carried it out. Watching their faces was a treat. 

Not that it was called for often, Marion ran a genteel establishment, a place for people to forget their problems rather than inviting new ones in. But you did have to be careful when you catered to people from the higher ranks of society, politicians and high richters and the like, people who were arrogant and used to getting their way. People like that could use reminders every so often.

Molly stuck his tongue out at Yasha before remembering her eyes were closed, then loudly announcing, “I’m sticking my tongue out at you!”

Yasha waggled her fingers at him in response, “Get to work.”

Molly flicked his tail and did, sauntering into the bar room like he absolutely definitely wasn’t incredibly late. It looked the same as it did most weekday nights. Not their busiest but respectably full, more than half the tables occupied by either a small group or a couple and there were several bodies at the bar. 

Red was the theme of the room but it was a seamless sea of different kinds of red that all came together perfectly to make the room feel bright, lively, like a beating heart. The lights were kept intimate, singular globes above the tables and enough golden hangings and trinkets and glass bottles behind the bar to catch it and throw it where it was needed. 

Molly saw familiar faces everywhere, his family. He saw Beau leaning forward to give the blushing court musician across from her a good view down her top, kissing her manicured, painted nails. He saw Fjord, who didn’t work here but had been on shore for a while now, sat at the bar with a tankard of his favourite and a book on the marbled countertop.

Molly considered going over there and offering him his services for the night. Fjord was kind, gentle but an absolutely fantastic lay and a good friend besides. 

“You’re late.” 

Molly cursed under his breath and turned to find Marion sat in her favourite booth just behind him. He hadn’t even had time to check. 

“I slept in, Marion, I’m sorry,” he gave a disarming, amiable smile. And it was true, he’d put his head down for a nap that afternoon and it had become five solid hours of sleep. 

Marion leaned forward, her expression unimpressed but not angry, “And have you checked the call book to see if you have an appointment tonight?”

Molly’s expression gave the answer for him and he looked down at his feet. 

“My little amethyst…”

“I know, I know, okay?” Molly cut across her desperately. Anger or annoyance he could deal with, the gentle tone of disappointment was unbearable, “I messed up. It won’t happen again.”

Marion fixed him with her golden eyes, the ones that seemed to never be still, like gold dust was constantly caught in eddies and currents behind her long lashes. She must have judged he was suitably chastised as she rose from her place and came to pat his cheek gently.

“Good. Because you do have an appointment tonight and it’s a very important one.” 

Curiosity piqued, Molly trotted after her, back into the foyer. Yasha opened one eye to smirk at him pointedly and he favoured her with a middle finger, quickly put away before Marion could see. 

“Who have I got?” Molly peered at the open call book in Marion’s hand, where any pre-arranged sessions with a specific courtesan were recorded, along with their time, price and any special requests.

Molly spent most of his time with requests like this. He’d build himself something of a reputation in Zadash, he could be considered half a prince in his line of work and his time was often sought. 

“Someone very important,” Marion tapped her fingers on his wrist gently, “I need your full attention, love, okay?”

“You’ve got it!” Molly insisted, trying to look attentive. Difficult, given that everything about him gave off an air of laissez-faire flightiness. 

Marion gave him a look, making him smile crookedly before flipping to today’s page. Her handwriting was impeccable, everything done in looping red ink. 

“He’s a new client,” she explained, still using her firm, ‘this is very important so don’t mess it up Molly’ voice, “Seems shy. Awkward about calling, you know how they are at first.”

Molly nodded. He did know. They came in two kinds, hiding their awkwardness to be hiring courtesans behind bluster and arrogance or honestly, openly embarrassed, all sweaty palms and darting eyes, showing up to the brothel with their hoods up. Both kinds soon lost that or they didn’t become recurring customers. 

“Who is he?” Molly asked, playing with a bangle on his wrist. They were always someone. 

“An archmage.” 

That caught his attention. No one was more powerful in the city of Zadash than the council of ten archmages that presided over them, protecting the citizens with depths of magic not open to anyone else. It was hard to think of them as being like the other politicians, the richters and lawmakers and captains. It was hard to think of one wanting the services of a sex worker. 

“Has he got a pointy hat covered in stars and a beard down to his feet?” he asked, imagining something from a storybook. 

Marion rolled her eyes, “Now Mollymauk. He’s not like that, he’s young. Very much so, in fact, he’s the youngest to get the title in living memory. And he sounded sweet over the message.”

“So what does he need?” 

“Someone kind and gentle. Someone willing to hold his hand and tell him everything’s okay,” Marion said without pause. She’d been in the business longer than anyone, she knew what anyone who passed that red lead lantern outside her door needed. 

Molly smiled, he liked jobs like that, “Sure. I can manage that.” 

“Good because he’ll be here in five,” Marion patted his chest, sweeping off to do one of the many minute tasks the brothel needed to keep running as smoothly as he did. 

“In five minutes?” Molly yelped, “That soon?”

“Like I said,” Marion called dismissively as she swept through the curtain of silk to her office, “You’re late.” 

Molly decided it would be best not to meet his new friend in the bar, if he was going to spook so easily. Quite often, with courtesans milling around with unclaimed clients, low light, alcohol flowing and the aphrodisiac herb Marion had sprinkled into the incense burners, there would be two or several people already beginning the fun part of their nights in the bar area. 

Instead, he had Yasha direct the archmage upstairs when he arrived, up to his private rooms. Every worker at the brothel had a suite in the almost impossibly tall house, the first room of which was for entertaining clients with décor that blended perfectly with the rest. But beyond that would be their own private rooms where they lived and spent their free hours. 

Molly quickly bustled around in his, lighting candles and pouring out two large glasses of wine. He clapped his hands and soft music instantly filled the room, low and unobtrusive but light, as perfect as the scent of cinnamon and vanilla that quickly billowed around the room. He had just enough time to look down at himself and decide that the black lingerie set under a gauzy, billowing gold wrap he was wearing was good enough before there was a knock at the door. 

Molly looked up and quickly scrambled to the bed, throwing himself semi seductively over it, before calling, “Come in.”

He didn’t look like he expected him to. 

He was very young, almost painfully skinny, made of all angles. Everything about him was an effort to hide, the overlarge coat he was drowning in, the rust red hair he’d allowed to grow over his face, the beard that hid whatever the hair didn’t. It was like a shy cat peering anxiously from under a bed. 

“My lord archmage,” Molly smiled, none of his surprise showing on his face, “Good evening. I was delighted to hear I was entertaining you tonight.” 

The man nodded, though it seemed like the title made him wince, “Just Caleb is fine, thanks.” 

“Caleb,” Molly repeated, rolling it over his tongue like a sweet, “A lovely name.” 

That made him blush more than he already was, if such a thing were possible, “Thanks. And you’re…Mollymauk, right.”

“Molly to my friends,” he smiled, rising and moving to take his hands, running his thumbs over his knuckles soothingly, “And we’re friends now, yes?”

“I suppose so. I know Beau, actually, we’re friends? She recommended I come here. She said I needed to interact more with things that weren’t books.”

Molly snorted, “Yes, that sounds like our dear Beauregard. I’m sure your work is fascinating, you’ll have to tell me all about it sometime. But for tonight I’m positive I can make a good distraction.” 

He winked and grinned. Always be light, flirty, teasing. Be fun. 

His new friend Caleb tried a smile but it flickered and died quickly, “Um…listen, I’m sorry but…I’m not very experienced?” 

Molly smiled kindly, “First time paying someone for sex? Or just first time?”

With how hard someone so young would have to work to become an archmage, he wouldn’t be surprised if there had been no time for romancing. 

Caleb shifted awkwardly, “Not first time. I, uh, I had a boyfriend in university? But yeah, that was a very…very long time ago.”

Molly found himself liking this man a lot, he was cute and genuine, more so than anyone had been with him in a while. 

“Well, I can guide you, sweetling, that’s no problem,” he patted his arm, leading him to the bed, “And we’ll keep communicating the whole way through so if anything happens you don’t like, just let me know and it’ll stop straight away.” 

Caleb looked visibly relieved at that affirmation, nodding hard. He finally tucked his hair behind his ears, revealing his face fully. Molly considered it a small victory. 

“You’re a handsome man, you know,” he said honestly, patting one rough cheek, “And your accent is so lovely. Where’s it from?”

“The Zemni Fields,” Caleb smiled, “Same to you, where’s yours from?”

Molly was thrown by that. The short answer was that he had no idea. 

So he did what he always did when he had nothing prepared. He smiled and batted his eyelashes. 

“Oh, middle of nowhere,” Molly shrugs, “But I’ve been here so long I’m practically local. But more importantly…” he leaned in close, knowing fine well his intoxicating perfume would be filling his nose and his full chest would be visible as the wrap came away, “What can I do to give you a wonderful night?”

Caleb thought for a while, looking down at his hands, “I…I think I’d like you to show me what makes you feel good?”

Mollymauk had heard some spectacularly weird, wonderful answers to that question. But he’d never heard that. 

“Me?” he blinked, “Not to be too forward, Caleb, but you’re the one whose paying for this?”

The rumpled looking wizard shrugged, hands disappearing up his large sleeves, “And you’re the one that does this with people over and over every day, having to do everything they want to do. I guess…I want to give you the choice?” 

Molly actually sat back a little, eyes wide. After a few moments, a smile sparked on his face. 

“You’re a funny one, Caleb. But I like you. And hell, if you’re offering to finger me, I’m not about to say no.” 

This time, Caleb did smile.

Molly sighed contentedly, lying against the soft pillows his work bed had come fully fitted with. Some nights he just slept here instead, the sheets were softer. 

Caleb crouched between his spread legs, all clothes abandoned aside from his billowing white shirt. Somehow the attempt at preserved modesty, the way the fabric kept sliding up to reveal the curve of his ass or the darker thicket of red hair between his thighs, it was more tantalising than if he’d just stripped entirely. Getting him to that level had taken so much coaxing and reassuring.

“These are beautiful,” Caleb sounded awed, stroking the ink that ran across Mollymauk’s skin with reverent fingers. 

“Thanks,” the tiefling was especially proud of his tattoos. Most of his pay went on adding to them whenever an idea struck him. It helped that he got discounts, seeing as his artist was a regular client. 

“What do they all mean?” Caleb asked, fascinated. 

“It’s a long story,” Molly brought his tail up to curl around Caleb’s leg loosely, “Maybe one day if you find them all and kiss them all, I’ll tell you.” 

That idea clearly pleased Caleb, given how his eyes widened and sparked with energy. He had him for another appointment, Molly was certain.

“Now,” he made his voice low and gentle, though no less a command, “Let your fingers wander where they want at first. Touch all of me.”

Caleb obeyed, moving further forward on his knees and letting his hand drift to the heat between Molly’s spread thighs. His fingers were like the rest of him, shy and hesitant, but so, so sweet. Molly made sure to let him know it, moaning as soon as the pads of his fingers began to trace the folds of him. 

“You’re so wet…” Caleb gasped.

“Because I want you so badly,” Molly groaned, shivering with longing, “Oh, right there…touch me right there…”

Under his whimpered, moaned instruction, Caleb’s shy ministrations soon grew more confident and before long, Molly was twisting under his thumb, pressed right against his clit.

“Harder…” the tiefling panted, chest heaving, “Fuck, I’m close…”

Caleb grinned, “You’re so beautiful like this. Can you…I want to watch…”

Molly nodded, one violet curl fallen artfully across his flushed face. He threw back his head and screamed out his relief, soaking Caleb’s fingers and a good portion of the sheets underneath them. 

And in the moment after, in that still, suspended moment where nothing felt quite real and everything held its breath, Caleb bent and kissed him. 

And it was kind of perfect.

“Did I do good?” Caleb asked shyly, legs folded underneath him as he sat back. 

“You did incredibly,” Molly assured him, still collecting his breath back, unsurprised that Caleb seemed to live for any kind of validation. He’d have to remember that for another night; for now, their hour was up.

And there would be other nights. He knew that for a certainty, as he cleaned himself up and helped Caleb redress. He could see the look on his face. 

Molly watched from the window as Caleb stepped back onto the street, now dark and lit only by the moon. 

He had a feeling he’d be seeing a lot more of Caleb Widogast. 

**Author's Note:**

> Find me on Tumblr, @mollymauk-teafleak


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